4-Toluenesulfonyl chloride → 1-(4-Toluenesulfonyl)-4-hydroxy-D-proline

Participants

Reaction Steps

To 10 g (76.30 mmol) of 4-hydroxy-D-proline in 75 ml of water was added 17.45 g (91.6 mmol) of 4-toluenesulfonyl chloride and 17 g (160.2 mmol) of sodium carbonate and the mixture was allowed to stir for 24 hours at room temperature. The reaction was then acidified to pH 1 by the careful addition of 10% aqueous HC1 solution and the product was isolated by filtration. After drying at high vacuum, 18.5 g of product was isolated (85% yield). M.P.=145°-146° C.

Provenance & Evidence